Deeper cavitands

Journal of Organic Chemistry

Volumn 64, Issue 12, 1999, Pages 4555-4559

  Tucci, Fabio C ^a   Rudkevich, Dmitry M ^a   Rebek Jr , Julius ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADAMANTANE DERIVATIVE; CAPROLACTAM DERIVATIVE; CYCLOHEXANE DERIVATIVE; RESORCINOL DERIVATIVE;

ARTICLE; CHEMICAL BINDING; COMPLEX FORMATION; CONFORMATIONAL TRANSITION; CYCLIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0033546216     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990209z     Document Type: Article

References (49)

1. (a) Cram, D. J. Science 1983, 219, 1177-1183.
2. (b) Cram, D. J.; Cram, J. M. Container Molecules and their Guests; Royal Society of Chemistry: Cambridge, 1994; pp 85-130.
3. (a) Högberg, A. G. S. J. Am. Chem. Chem. 1980, 102, 6046-6050.
4. (b) Högberg, A. G. S. J. Org. Chem. 1980, 45, 4498-4500.
5. (c) Tunstad, L. M.; Tucker, J. A.; Dalcanale, E.; Weiser, J.; Bryant, J. A.; Sherman, J. C.; Helgeson, R. C.; Knobler, C. B.; Cram, D. J. J. Org. Chem. 1989, 54, 1305-1312. For a timely review, see: Timmerman, P.; Verboom, W.; Reinhoudt, D. N. Tetrahedron 1996, 52, 2663-2704.
6. (c) Tunstad, L. M.; Tucker, J. A.; Dalcanale, E.; Weiser, J.; Bryant, J. A.; Sherman, J. C.; Helgeson, R. C.; Knobler, C. B.; Cram, D. J. J. Org. Chem. 1989, 54, 1305-1312. For a timely review, see: Timmerman, P.; Verboom, W.; Reinhoudt, D. N. Tetrahedron 1996, 52, 2663-2704.
7. (a) Cram, D. J.; Karbach, S.; Kim, H.-E.; Knobler, C. B.; Maverick, E. F.; Ericson, J. L.; Helgeson, R. C. J. Am. Chem. Soc. 1988, 110, 2229-2237.
8. (b) Cram, D. J.; Stewart, K. D.; Goldberg, I.; Trueblood, K. N. J. Am. Chem. Soc. 1985, 107, 2574-2575.
9. (c) Tucker, J. A.; Knobler, C. B.; Trueblood, K. N.; Cram, D. J. J. Am. Chem. Soc. 1989, 111, 3688-3699.
10. (d) Moran, J. R.; Karbach, S.; Cram, D. J. J. Am. Chem. Soc. 1982, 104, 5826-5828.
11. (e) Moran, J. R.; Ericson, J. L.; Dalcanale, E.; Bryant, J. A.; Knobler, C. B.; Cram, D. J. J. Am. Chem. Soc. 1991, 113, 5707-5714.
12. (f) Cram, D. J.; Choi, H. J.; Bryant, J. A.; Knobler, C. B. J. Am. Chem. Soc. 1992, 114, 7748-7765.
13. (a) Dalcanale, E.; Soncini, P.; Bacchilega, G.; Ugozzoli, F. J. Chem. Soc., Chem. Commun. 1989, 500-502.
14. (b) Soncini, P.; Bonsignore, S.; Dalcanale, E.; Ugozzoli, F. J. Org. Chem. 1992, 57, 4608-4612.
15. (c) Dalcanale, E.; Costantini, G.; Soncini, P. J. Inclusion Phenom. Mol. Recognit. Chem. 1992, 13, 87-92.
16. Gas-phase complexation studies: (a) Vincenti, M.; Dalcanale, E.; Soncini, P.; Guglielmetti, G. J. Am. Chem. Soc., 1990, 112, 445-447.
17. (b) Vincenti, M.; Minero, C.; Pelizzetti, E.; Secchi, A.; Dalcanale, E. Pure Appl. Chem. 1995, 67, 1075-1084.
18. (b) Dickert, F. L.; Baumler, U. P. A.; Stathopulos, H. Anal. Chem. 1997, 69, 1000-1005.
19. Schierbaum, K. D.; Weiss, T.; Thoden van Velzen, E. U.; Engbersen, J. F. J.; Reinhoudt, D. N.; Gopel, W. Science 1994, 265, 1413.
20. (a) Rudkevich, D. M.; Hilmersson, G.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 12216-12225.
21. (b) Rudkevich, D. M.; Hilmersson, G.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 9911-9912.
22. Kazimierczuk, Z.; Dudycz, L.; Stolarski, R.; Shugar, D. Nucleosides Nucleotides 1981, 8, 101-117.
23. Boger, D. L.; Panek, J. S.; Yasuda, M. Org. Synth. 1987, 66, 142-150.
24. (a) Wärnmark, K.; Thomas, J. A.; Heyke, O.; Lehn, J. M. Chem. Commun. 1996, 701-702.
25. (b) Warrener, R. N.; Butler, D. N.; Russel, R. A. Synlett 1998, 566-595.
26. Mohamadi, F.; Richards, N. G.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467.
27. For other approaches towards deep cavitands, see: (a) von dem Bussche-Hünnefeld, C.; Bühring, D.; Knobler, C. B.; Cram, D. J. Chem, Commun. 1995, 1085-1086. (b) von dem Bussche-Hünnefeld, C.; Helgeson, R. C.; Bühring, D.; Knobler, C. B.; Cram, D. J. Croat. Chem. Acta 1996, 69, 1447-458.
28. For other approaches towards deep cavitands, see: (a) von dem Bussche-Hünnefeld, C.; Bühring, D.; Knobler, C. B.; Cram, D. J. Chem, Commun. 1995, 1085-1086. (b) von dem Bussche-Hünnefeld, C.; Helgeson, R. C.; Bühring, D.; Knobler, C. B.; Cram, D. J. Croat. Chem. Acta 1996, 69, 1447-458.
29. (c) Ma, S.; Rudkevich, D. M.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 4977-4981. For extended calix[4]arene-resorcinarene-based surfaces, see: (a) Timmerman, P.; Nierop, K. G. A.; Brinks, E. A.; Verboom, W.; van Veggel, F. C. J. M.; van Hoorn, W. P.; Reinhoudt, D. N. Chem. Eur. J. 1995, 1, 132-143.
30. (c) Ma, S.; Rudkevich, D. M.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 4977-4981. For extended calix[4]arene- resorcinarene-based surfaces, see: (a) Timmerman, P.; Nierop, K. G. A.; Brinks, E. A.; Verboom, W.; van Veggel, F. C. J. M.; van Hoorn, W. P.; Reinhoudt, D. N. Chem. Eur. J. 1995, 1, 132-143.
31. (b) Higler, I.; Timmerman, P.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1996, 61, 5920-5931.
32. (c) Higler, I.; Verboom, W.; van Veggel, F. C. J. M.; Jong, F. de; Reinhoudt, D. N. Liebigs Ann./Recl. 1997, 1577-1586. For deep calix[4]arenes, see:
33. (d) Juneja, R. K.; Robinson, K. D.; Johnson, C. P.; Atwood, J. L. J. Am. Chem. Soc. 1998, 115, 3818-3819 and references therein.
34. (e) Xu, B.; Miao, Y.-J.; Swager, T. M. J. Org. Chem. 1998, 63, 8561-8564 and references therein.
35. 70 complexations with calixarenes in solution, see: (a) Haino, T.; Yanase, M.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 259-260. (b) Raston, C. L.; Atwood, J. L.; Nichols, P. J.; Sudria, I. B. N. Chem. Commun. 1996, 2615-2616.
36. 70 complexations with calixarenes in solution, see: (a) Haino, T.; Yanase, M.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 259-260. (b) Raston, C. L.; Atwood, J. L.; Nichols, P. J.; Sudria, I. B. N. Chem. Commun. 1996, 2615-2616.
37. (c) Araki, K.; Akao, K.; Ikeda, A.; Suzuki, T.; Shinkai, S. Tetrahedron Lett. 1996, 37, 73-76.
38. (d) Ikeda, A.; Yoshimura, M.; Shinkai, S. Tetrahedron Lett. 1997, 38, 2107-2110.
39. (e) Ikeda, A.; Suzuki, Y.; Yoshimura, M.; Shinkai, S. Tetrahedron 1998, 54, 2497-2508.
40. (f) Atwood, J. L.; Barbour, L. J.; Raston, C. L.; Sudria, I. B. N. Angew. Chem., Int. Ed. Engl. 1998, 37, 981-983.
41. (g) Haino, T.; Yanase, M.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1998, 37, 997-998.
42. (h) Wang, J.; Gutsche, C. D. J. Am. Chem. Soc. 1998, 120, 12226-12231.
43. 70 complexations with cyclotriveratrylene (CTV), see:
44. (j) Steed, J. W.; Junk, P. C.; Atwood, J. L.; Barnes, M. J.; Raston, C. L.; Burkhalter, R. S. J. Am. Chem. Soc. 1994, 116, 10346-10347.
45. 70 complexation by other resorcinarene-based cavitands, see ref 7a.
46. 70 did not show the molecular ions for the complexes.
47. The results obtained through the Benesi-Hildebrand equation were confirmed by the use of a nonlinear regression analysis curve-fitting software developed in the laboratories of Prof. François N. Diederich at ETH, Zürich.
48. For details on high-resolution mass spectrometry, see: (a) Rose, M. E.; Johnstone, R. A. W. Mass Spectrometry for Chemists and Biochemists; Cambridge University Press: Cambridge, 1982.
49. (b) Jennings, K. R.; Dolnikowsi, G. G. Methods in Enzymology, McCloskey, J. A., Ed.; Academic Press: New York, 1990; p 37 and references therein.